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Your Chesapeake Holiday
Lock in a Chesapeake holiday package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake holiday is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.
Greenbrier combines suburban comfort with retail convenience in this family-friendly Chesapeake area. Greenbrier Mall anchors the area with department stores and speciality shops alongside tree-lined residential streets. Parks and green spaces like Chesapeake Arboretum offer peaceful breaks from shopping. Explore Chesapeake City Park's walking trails or visit Oak Grove Lake Park for outdoor recreation. Chain restaurants and familiar stores line Greenbrier Parkway in typical American strip mall fashion. With limited public transit, having a car makes it easier to discover this authentic slice of suburban America.
Great Bridge offers a peaceful suburban retreat where Revolutionary War history meets waterfront tranquility. The area surrounds the scenic Intracoastal Waterway, with tree-lined streets leading to waterside parks and fishing piers. History buffs will appreciate the Great Bridge Battlefield & Waterways Museum commemorating a key Revolutionary War battle. Stroll along Elizabeth River's peaceful banks or enjoy a round at Chesapeake Golf Club. The family-friendly area features convenient shopping centers and casual seafood restaurants specialising in Chesapeake Bay delicacies. Though limited in public transit, the welcoming community provides an authentic glimpse into suburban American life.
Western Branch North offers a peaceful family-oriented residential retreat just outside Chesapeake's urban core. This welcoming area features tree-lined streets with colonial-style homes and manicured lawns. Travellers will appreciate the authentic suburban American experience without tourist crowds. The area provides easy access to Chesapeake Square Mall and Bowlero Western Branch for entertainment options. Nearby Elizabeth River natural areas offer opportunities for hiking, fishing, and kayaking. With affordable dining at casual eateries and comfortable holiday rentals, Western Branch North serves as an excellent base for budget-conscious travellers exploring the region.
South Norfolk blends historic charm with quiet suburban living. The tree-lined streets showcase early 20th-century Craftsman bungalows and Colonial Revival homes with inviting front porches. Visitors can explore the restored railway station and vintage shopfronts along Chesapeake Avenue. The area offers a genuine small-town Southern experience. Local diners serve comfort food while antique shops house unique regional treasures. Community parks provide peaceful retreats under towering pines, perfect for travellers seeking authentic local character away from tourist crowds.
Discover the most popular places to visit in Chesapeake
Greenbrier Mall
8.4/10 (837 reviews)
This regional shopping centre features over 100 stores and eateries, plus a Cinema Café for dining during films. Families enjoy the supervised soft play area and convenient amenities while shopping.
Chesapeake Square Mall blends shopping with entertainment at its 12-screen Cinemark XD theatre. Visit weekday mornings for a relaxed experience at this regional retail centre undergoing a $30 million revitalisation.
This versatile 39,000-square-foot venue hosts elegant weddings to professional conferences in Chesapeake, Virginia. The on-site catering team delivers customised dining experiences with free Wi-Fi and parking.
This sprawling 90-acre recreational haven hosts Chesapeake's signature events like the Jubilee and Symphony Under the Stars. Families enjoy the Fun Forest Playground and peaceful walking trails.
Lake Drummond, one of only two natural freshwater lakes in Virginia, sits at the heart of Great Dismal Swamp. Paddle through tea-colored waters while spotting black bears and rare birds in this serene ecosystem.
Encircling a serene 65-acre lake, this park's 1.5-mile trail offers picturesque views and abundant wildlife. Enjoy fishing from accessible platforms or relax at shaded picnic areas overlooking the water.
This semi-private course challenges golfers with strategic water hazards and unique doglegs through mature trees. Book morning tee times to experience the outstanding greens at their finest.
Learn about the local history of Chesapeake when you take a trip to Chesapeake Veterans' Memorial. Stroll along the area's beautiful beaches or experience its great live music.
"I didn’t like the fact that there were no updated tv in our room….when I reported a problem to the staff they did nothing to replace it. I didn’t like that the bed was so uncomfortable that I couldn’t sleep, And there was one elevator working the whole time I was there!!!"
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chesapeake, Virginia, is perfect for family, outdoor, and romantic getaways. Visitors can enjoy a scenic boardwalk, vibrant shopping centres, and a variety of fun tours. Outdoor activities abound, alongside Gulf Coast trips and holiday events, making it an ideal destination for all types of travellers seeking adventure and relaxation.
Shopping
In Chesapeake, you can visit Greenbrier Mall for a vibrant shopping experience with various shops and entertainment options. Cedar Lakes Retail Center offers a mix of family-friendly stores. If you're up for a drive, check out Chesapeake Square Mall for more shopping and entertainment.
Recreation
Harbor Park, a vibrant sports stadium, offers an energetic atmosphere perfect for enjoying live sports. Commodore Theatre provides a charming cinematic experience with family-friendly films and romantic options. The NorVa, an exciting music venue, showcases diverse performances, ensuring an entertaining evening filled with great tunes.
Adventure
Experience the great outdoors at Northwest River Park and Campground with camping and nature trails, embrace family fun at Jillian's Billiards arcadeAdventureZone, or indulge in some indoor sports at Folkes - Stevens Indoor Tennis Center, located 12.9km from Chesapeake, perfect for an adventurous day out.
Nightlife
Chesapeake's nightlife offers a vibrant mix of bars and live music. Visit the Greenbrier Bar and Grill for delightful cocktails, or enjoy local bands at the Chesapeake Music Hall. For a relaxed atmosphere, the Craft Beer Cellar is perfect for sampling unique brews with friends.
Find the best attractions in and around Chesapeake
Chesapeake, Virginia, offers a delightful blend of family-friendly activities, outdoor adventures, and romantic getaways. Visitors can explore urban parks, maritime museums, and historic college campuses, catering to those seeking culture and nature. With nearby attractions, beautiful beaches, and noteworthy sites, Chesapeake promises an enriching experience for all types of travellers looking to immerse themselves in local charm.
USS Wisconsin BB-64: This remarkable maritime museum offers a unique glimpse into naval history aboard one of the last battleships commissioned by the U.S. Navy. You can explore the ship’s decks, admire its impressive armaments, and gain insight into life at sea during wartime, all while soaking up the cultural vibes it exudes.
Lake Drummond: Nestled within Chesapeake, Lake Drummond is a picturesque spot perfect for outdoor enthusiasts. Enjoy scenic walks along the shoreline, indulge in romantic picnics, or simply bask in the tranquil beauty of nature, making it an ideal retreat for relaxation and adventure.
Pagoda and Oriental Garden: A hidden gem, this private garden enchants visitors with its historical charm and serene environment. Stroll through beautifully landscaped grounds adorned with traditional Asian architecture, offering a peaceful escape and a chance to reflect on the rich history it represents.
Best time to go to Chesapeake
The best time to visit Chesapeake is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Chesapeake
Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Chesapeake during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.
Frequently Asked Questions
Why should I book my Chesapeake holiday with Expedia?
With top-value flights, car hire and accommodation options all in one convenient place, Expedia makes arranging your Chesapeake break simple. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from awesome stays, add your flights and/or a hire car (and maybe also some exciting tours and activities!) and get unbeatable prices. Want to change your plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, check out our Customer Service Portal link.
When is the best time of year to holiday in Chesapeake?
If you'd like to experience the vibe of Chesapeake in peak season, plan your getaway for March, May and August. December, January and February are generally the quietest months of the year. To get an idea of the type of weather to expect, the average daytime temperature in January, the coolest month in Chesapeake, is 4ºC. The warmest month here is July, when temperatures average 26ºC.
What are the top hotels for my holiday in Chesapeake?
Bundle your flights and hotels with Expedia to save on your next big adventure. With more than 400 airlines and 321,000 hotels across the world, your Chesapeake holiday can be tailored exactly to suit your travel style. With all that extra money, why not include some awesome activities and tours? It's an easy way to unlock even more discounts. That dream holiday to Chesapeake is closer than you thought! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What is the best area to stay in when on holiday in Chesapeake?
If you plan to visit Greenbrier Mall, maximise your time sightseeing and find a place to stay close by. It's one of the most popular attractions in Chesapeake.
Do I need a visa for my Chesapeake holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for tourism or work, will determine if you need a visa for Chesapeake. Also be sure that your passport is up to date and has a minimum of six months validity remaining beyond your intended return date. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Chesapeake holiday?
First, consider the activities planned during your holiday in Chesapeake and choose versatile pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, look up style blogs or relevant social media accounts. Pack your luggage with confidence by monitoring the weather forecast in Chesapeake. July brings the warmest temperatures, with daily averages of 26ºC, while January days average 4ºC, making it the coolest time of year.
What does an Expedia Chesapeake holiday include?
Flights, car hires and hotels, or any combination of the three — the choice is yours. Whether you're headed to Chesapeake with the whole family or enjoying a solo break, there's a bundle to suit every style and budget. Once you've made your booking, why not add on one or two tours and experiences? Private holiday homes and apartments are a couple of the most highly sought-after property types in Chesapeake. Whatever your group size or holiday style, you can rely on Expedia for the freedom and flexibility to customise your next big adventure.
Does Expedia offer Book Now, Pay Later Chesapeake holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:
Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient payment plans. If paying across multiple instalments sounds right for you, choose this option at checkout.
No-deposit holidays: Pressing the "book now" button is easier with this payment option. With no deposit required for your escape, you can Book Now, Pay Later and start working on your travel plans.
Can I choose my airline with a Chesapeake Expedia holiday?
Yes — that's one of the best things about an Expedia holiday package. You're in control. We have more than 400 airline partners around the world, so you have lots of choice when putting together your Chesapeake adventure.